Save $100 on nonstop flights from Chicago to San Juan, Puerto Rico. Fares are now just $274 roundtrip, including taxes. Fare Calendar:

Note: JetBlue charges $20-$25 for the first checked bag when booking their lowest fare class (Blue). American and United charge $25 for the first checked bag. Check our baggage fee chart for more information.


  • $100 OFF the usual cost

Travel Dates:

  • Through May 24

Sample Screenshots:

Chicago to San Juan: Results

Chicago to San Juan: Results

Chicago to San Juan: Booking Page

Chicago to San Juan: Booking Page Updates

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Featured Image: San Juan, Puerto Rico at Night (

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